2.0 2012-10-10 12:22:43 -0600 2015-08-05 16:22:04 -0600 ECMDB23222 M2MDB003612 NMN 3-Carbamoyl-1-beta-D-ribofuranosyl pyridinium hydroxide-5'phosphate, inner salt. A nucleotide in which the nitrogenous base, nicotinamide, is in beta-N-glycosidic linkage with the C-1 position of D-ribose &beta;-nicotinamide mononucleotide &beta;-nicotinamide nucleotide &beta;-nicotinamide ribonucleotide NicRN NMN C11H16N2O8P 335.2271 335.06442701 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium 1094-61-7 [H][C@]1(COP(O)(O)=O)O[C@@]([H])([N+]2=CC=CC(=C2)C(O)=N)[C@]([H])(O)[C@]1([H])O InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/p+1/t7-,8-,9-,11-/m1/s1 DAYLJWODMCOQEW-TURQNECASA-O Solid Cytoplasm mitochondria nucleus logp -1.50 ALOGPS logs -2.31 ALOGPS solubility 1.80e+00 g/l ALOGPS logp -6.2 ChemAxon pka_strongest_acidic 1.21 ChemAxon pka_strongest_basic -1.6 ChemAxon iupac 3-carbamoyl-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-[(phosphonooxy)methyl]oxolan-2-yl]-1lambda5-pyridin-1-ylium ChemAxon average_mass 335.2271 ChemAxon mono_mass 335.06442701 ChemAxon smiles [H][C@]1(COP(O)(O)=O)O[C@@]([H])([N+]2=CC=CC(=C2)C(O)=N)[C@]([H])(O)[C@]1([H])O ChemAxon formula C11H16N2O8P ChemAxon inchi InChI=1S/C11H15N2O8P/c12-10(16)6-2-1-3-13(4-6)11-9(15)8(14)7(21-11)5-20-22(17,18)19/h1-4,7-9,11,14-15H,5H2,(H3-,12,16,17,18,19)/p+1/t7-,8-,9-,11-/m1/s1 ChemAxon inchikey DAYLJWODMCOQEW-TURQNECASA-O ChemAxon polar_surface_area 163.42 ChemAxon refractivity 71.71 ChemAxon polarizability 29.05 ChemAxon rotatable_bond_count 5 ChemAxon acceptor_count 7 ChemAxon donor_count 5 ChemAxon physiological_charge -1 ChemAxon formal_charge 1 ChemAxon Nicotinate and nicotinamide metabolism ec00760 DNA replication eco03030 Metabolic pathways eco01100 NAD salvage Even though NAD molecules are not consumed during oxidation reactions, they have a relatively short half-life. For example, in E. coli the NAD+ half-life is 90 minutes. Once enzymatically degraded, the pyrimidine moiety of the molecule can be recouped via the NAD salvage cycles. This pathway is used for two purposes: it recycles the internally degraded NAD products nicotinamide D-ribonucleotide (also known as nicotinamide mononucleotide, or NMN) and nicotinamide, and it is used for the assimilation of exogenous NAD+. NAD reacts spontaneously with water resulting in the release of hydrogen ion, AMP and beta-nicotinamide D-ribonucleotide. This enzyme can either interact spontaneously with water resulting in the release of D-ribofuranose 5-phosphate, hydrogen ion and Nacinamide. On the other hand beta-nicotinamide D-ribonucleotide can also react with water through NMN amidohydrolase resulting in ammonium, and Nicotinate beta-D-ribonucleotide. Also it can interact with water spontaneously resulting in the release of phosphate resulting in a Nicotinamide riboside. Niacinamide interacts with water through a nicotinamidase resulting in a release of ammonium and nicotinic acid. This compound interacts with water and phosphoribosyl pyrophosphate through an ATP driven nicotinate phosphoribosyltransferase resulting in the release of ADP, pyrophosphate and phosphate and nicotinate beta-D-ribonucleotide. Nicotinamide riboside interacts with an ATP driven NadR DNA-binding transcriptional repressor and NMN adenylyltransferase (Escherichia coli) resulting in a ADP, hydrogen ion and beta-nicotinamide D-ribonucleotide. This compound interacts with ATP and hydrogen ion through NadR DNA-binding transcriptional repressor and NMN adenylyltransferase resulting in pyrophosphate and NAD. Nicotinate beta-D-ribonucleotide is adenylated through the interaction with ATP and a hydrogen ion through a nicotinate-mononucleotide adenylyltransferase resulting in pyrophosphate and Nicotinic acid adenine dinucleotide. Nicotinic acid adenine dinucleotide interacts with L-glutamine and water through an ATP driven NAD synthetase, NH3-dependent resulting in AMP, pyrophosphate, hydrogen ion, L-glutamic acid and NAD. PW000830 Metabolic Specdb::CMs 35350 Specdb::CMs 47836 Specdb::CMs 162072 Specdb::NmrOneD 6192 Specdb::NmrOneD 6193 Specdb::NmrOneD 6194 Specdb::NmrOneD 6195 Specdb::NmrOneD 6196 Specdb::NmrOneD 6197 Specdb::NmrOneD 6198 Specdb::NmrOneD 6199 Specdb::NmrOneD 6200 Specdb::NmrOneD 6201 Specdb::NmrOneD 6202 Specdb::NmrOneD 6203 Specdb::NmrOneD 6204 Specdb::NmrOneD 6205 Specdb::NmrOneD 6206 Specdb::NmrOneD 6207 Specdb::NmrOneD 6208 Specdb::NmrOneD 6209 Specdb::NmrOneD 6210 Specdb::NmrOneD 6211 Specdb::MsMs 28391 Specdb::MsMs 28392 Specdb::MsMs 28393 Specdb::MsMs 34949 Specdb::MsMs 34950 Specdb::MsMs 34951 Specdb::MsMs 2352172 Specdb::MsMs 2352173 Specdb::MsMs 2352174 HMDB00229 14180 C00455 16171 NICOTINAMIDE_NUCLEOTIDE NMN FDB021912 Protein ushA P07024 USHA_ECOLI ushA http://ecmdb.ca/proteins/P07024.xml Nicotinate-nucleotide adenylyltransferase P0A752 NADD_ECOLI nadD http://ecmdb.ca/proteins/P0A752.xml Multifunctional protein surE P0A840 SURE_ECOLI surE http://ecmdb.ca/proteins/P0A840.xml 5'-nucleotidase yjjG P0A8Y1 YJJG_ECOLI yjjG http://ecmdb.ca/proteins/P0A8Y1.xml DNA ligase P15042 DNLJ_ECOLI ligA http://ecmdb.ca/proteins/P15042.xml DNA ligase B P25772 LIGB_ECOLI ligB http://ecmdb.ca/proteins/P25772.xml Transcriptional regulator nadR P27278 NADR_ECOLI nadR http://ecmdb.ca/proteins/P27278.xml NADH pyrophosphatase P32664 NUDC_ECOLI nudC http://ecmdb.ca/proteins/P32664.xml Nicotinamide-nucleotide amidohydrolase PncC P0A6G3 PNCC_ECOLI pncC http://ecmdb.ca/proteins/P0A6G3.xml NAD + (deoxyribonucleotide)(n) + (deoxyribonucleotide)(m) > Adenosine monophosphate + NMN + (deoxyribonucleotide)(n+m) Adenosine triphosphate + NMN > Pyrophosphate + NAD Adenosine triphosphate + Nicotinamide riboside > ADP + NMN NAD + Water > Adenosine monophosphate + NMN Water + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMN R00103 NADPYROPHOSPHAT-RXN Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide + NMN <> NAD + Pyrophosphate R00137 2.7.7.1-RXN NAD + DNA <> Adenosine monophosphate + NMN R00382 NMN + Water <> Nicotinamide ribotide + Ammonia R02322 beta-nicotinamide D-ribonucleotide + Water + NMN > Ammonium + nicotinate beta-D-ribonucleotide + Nicotinamide ribotide PW_R003017 Nicotinamide riboside + Adenosine triphosphate > Adenosine diphosphate + Hydrogen ion + beta-nicotinamide D-ribonucleotide + ADP + NMN PW_R003022 beta-nicotinamide D-ribonucleotide + Adenosine triphosphate + Hydrogen ion + NMN > Pyrophosphate + NAD PW_R003023 Water + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMN NMN + Water <> Nicotinamide ribotide + Ammonia Adenosine triphosphate + Hydrogen ion + Nicotinamide ribotide + NMN <> NAD + Pyrophosphate Water + NAD <> Adenosine monophosphate +2 Hydrogen ion + Nicotinamide ribotide + NMN